N-benzyl-N-methyl-L-tyrosine methyl ester | 866392-22-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzyl-N-methyl-L-tyrosine methyl ester
• 英文别名: Bn,Me-L-Tyr-OMe；methyl (2S)-2-[benzyl(methyl)amino]-3-(4-hydroxyphenyl)propanoate
• CAS: 866392-22-5
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: ZGRCTTHJKJZPRO-KRWDZBQOSA-N

物化性质

• 沸点：
  441.9±45.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-methyl-L-tyrosine methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以87%的产率得到N-benzyl-N-methyl-L-tyrosinol
  参考文献：
  名称：

  L-氨基酸的“ N-立体异构季铵盐”：合成，分离和绝对构型

  摘要：

  Abstractmagnified imageDiastereoisomeric linear and cyclic ‘N‐chiral quaternary ammonium salts’ (QASs) were efficiently synthesized from corresponding L‐amino acids in high yields. The diastereoisomers of each pair of ‘N‐chiral QASs’ were successfully separated. The absolute configurations of these QASs were determined predominately by X‐ray single‐crystal analysis. The 1H‐NMR data of ‘N‐chiral QASs’ provided characteristic information on the configuration of the N‐chiral center. ‘N‐Chiral QASs’ exemplified by [N(R)]‐2a and [N(S)]‐2a are stable in protic and aprotic solvents within a broad pH and temperature range.

  DOI：

  10.1002/hlca.200800326
• 作为产物：
  描述：

  methyl N-benzylidene-tyrosinate 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 39.0h， 生成 N-benzyl-N-methyl-L-tyrosine methyl ester
  参考文献：
  名称：

  无需侧链保护即可轻松合成高度官能化的N-甲基氨基酸酯。

  摘要：

  [反应：见正文]提出了一种通过还原胺化的简便，两锅法合成N-甲基氨基酸酯的方法。不需要侧链保护方案，起始原料都是可商购的，并且合成方法是直接的并且可以非常高的产率提供所需的产物。

  DOI：

  10.1021/ol051441w

文献信息

• Mild and Nonracemizing Conditions for Ullmann-type Diaryl Ether Formation between Aryl Iodides and Tyrosine Derivatives
  作者：Qian Cai、Gang He、Dawei Ma

  DOI：10.1021/jo0606960

  日期：2006.7.1

  [GRAPHICS]CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs2CO3 works at 90 degrees C to provide the corresponding diaryl ether. Partial racemization occurs when N-Boc- and N-Cbz-protected aromatic amino esters are used, while N-trityl-and N,N-dibenzyl-protected aromatic amino esters give rise to coupling products without loss of optical purity. Little racemization is also observed in cases of N-Boc- and N-Cbz- protected aromatic amino acids as substrates. But their reaction yields are moderate. On the basis of these studies, shorter protocols for assembling (S,S)-isodityrosine and K-13 are developed.